Senior Technical Solutions Consultant (Mid-Market & Enterprise)

15Five; United States; On-site; USD 170,000 - 210,000; Full time

Job summary

15Five is seeking a Technical Closer and Strategic Co-Pilot to partner with the revenue team across Mid-Market and Enterprise segments. You’ll validate requirements, navigate HRIS integrations, and translate HR philosophy into technical solutions for diverse organizations.

You will embed with AEs, drive technical closes, and prototype PoCs while addressing security and compliance in complex deals.

Qualifications

• Builder mindset with enthusiasm for product/API integrations.
• Ability to translate HR concepts for IT stakeholders.
• Experience partnering with sales teams to move deals forward.
• Comfortable handling security/compliance questionnaires (GDPR, SOC2, PII).

Responsibilities

• Embed in the sales cycle as a revenue partner to elevate deal strategy.
• Validate complex requirements and map solutions to prospects’ pain points.
• Lead strategic prep and push back to align demos with needs.
• Execute the Technical Close by removing remaining friction.
• Prototype POCs and build bespoke environments reflecting client culture.

Skills

Strategic deal strategy

Revenue partner mindset

API integration planning

HRIS integrations

Technical intro & close

Sales coordination

APIs & data flows

POC configuration

Security/compliance awareness

Tools

Postman

HRIS ecosystems (Workday, ADP, UKG)

Demo automation tools (Postman)

Salesforce

Gong

AI tools (Claude, ChatGPT)

Job description

• In this role, you will serve as the Technical Closer and Strategic Co-Pilot for 15Five’s revenue team, covering both Mid-Market and Enterprise segments
• You are not a “demo jockey”; you are a revenue partner and a solution builder
• Working alongside Account Executives (AEs), you will secure the “Tech Win” by validating complex requirements, navigating global HRIS integrations, and translating high-level HR philosophy into technical reality for organizations ranging from mid-sized disruptors to large-scale enterprises
• We are looking for an ambitious, high-grit professional who has a passion for building—whether that’s mapping out a complex API integration or shaping the “vibe” and functionality of a new product feature
• Reports to: VP, Revenue and Emerging AI
• 1. Strategic Co-Piloting & Deal Strategy (High Focus)
• Proactive Partnership: Embed yourself in the sales cycle as a revenue partner. Adapt to various sales styles and actively elevate deal strategy on every call, from quick-moving mid-market deals to long-cycle enterprise evaluations
• Prep Authority: Hold AEs accountable for deep discovery. You have the authority to “push back on prep” to ensure every demonstration is strategically aligned with the prospect’s pain points
• The “Cleanup” & Reality Checks: Skillfully manage expectations if a prospect has been over-promised. Diplomatically navigate workarounds that solve the core pain point without stalling the deal
• Closing: Recognize buying signals and execute the “Technical Close” by confidently removing any lingering technical friction
• 1. Technical Execution & Integration Building (High Focus)
• Segment-Specific Demonstrations: Conduct high-stakes demos tailored to the audience—from agile Mid-Market teams to complex Enterprise committees. Showcase edge cases, bespoke workflows, and “art of the possible” configurations that address global scale
• Integration Architecture & Construction: Serve as the authority on the HRIS ecosystem (Workday, UKG, ADP, etc.). You don’t just talk about data flows; you enjoy building and scoping API/SFTP integrations live to remove technical friction for IT stakeholders
• Product Prototyping: Act as a “builder” within the sales process. Configure bespoke Proof of Concepts (POCs) and environments that reflect the specific culture and “vibe” of a prospect’s organization, regardless of size
• Security & Compliance: Confidently navigate security questionnaires (GDPR, SOC2, PII) and enterprise-grade procurement processes without needing constant support from InfoSec
• 1. Content Creation & Market Intelligence (Medium Focus)
• Sales Enablement: Create “micro-demos” (Loom/Vidyard) and annotated assets to arm internal champions with the tools to sell 15Five when you aren’t in the room
• Voice of the Market: Act as a bridge between Sales and Product. Influence the roadmap by documenting product gaps, integration blockers, and “vibe” shifts in the market to ensure our product stays ahead of the curve

Tools You’ll Use

• Technical/Building: Postman (API testing), HRIS Ecosystem (Workday, ADP, UKG, etc.), Demo Automation Tools (Postman)
• Communication: Slack, Loom, Vidyard
• Sales/CRM: Salesforce, Gong
• AI: Claude, ChatGPT, Cursor, etc

Benefits

• Medical, dental, and vision care
• Fertility consulting assistance
• 24/7 online therapy assistance

The “Builder” Mindset: A genuine desire or experience in building products or API integrations. You enjoy the “how it works” as much as the “how it sells.”

Adaptability: Comfortable in a fast-paced environment where you may need to “call an audible” during a live demo or build a custom environment late in the day to keep a deal moving

HR Domain Empathy: Ability to speak the language of HR buyers (calibration, competency matrices, flight risk) and translate it for IT buyers

Sales Grit & Ambition: We value “hunger” over years of experience. You should view yourself as part of a sales engine, understanding deal velocity and urgency across different market segments

Integration Fluency: Demonstrated ability to work with APIs, SFTP, SSO, and data migration. You should be comfortable using tools like Postman to validate workflows

Eading over the role description and feeling like you don’t check every box? That’s okay; if you think you have what it takes but don’t necessarily meet all the criteria, please apply—you could be exactly who we are looking for!